ArticleProceedings of the National Academy of Sciences of the United States of America2024
Oxazolone mediated peptide chain extension and homochirality in aqueous microdroplets.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 20 citations in OpenAlex.
- Single droplet displacement infrared action spectroscopy.Nature communications · 2026Article
- Protopeptide backbone affects assembly in aqueous solutions.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Mechanisms of ionization and of chemical reactions in charged microdroplets.Chemical science · 2025Review
- Real-Time Visualization of an Elusive, Strong Reducing Agent during Tris(2,2'-bipyridyl)ruthenium(II) Electro-Oxidation in Water.Journal of the American Chemical Society · 2025Article
- Serine Octamer Clusters Direct the Chirality of Peptides Formed in Water Microdroplets.The journal of physical chemistry. A · 2025Article
- Interfacial electromigration for accelerated reactions.Analytica chimica acta · 2025Article
- Accelerated peptide bond formation at air-water interfaces.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Peptide formation from amino acids is thermodynamically unfavorable but a recent study provided evidence that the reaction occurs at the air/solution interfaces of aqueous microdroplets. Here, we show that i) the suggested amino acid complex in microdroplets undergoes dehydration to form oxazolone; ii) addition of water to oxazolone forms the dipeptide; and iii) reaction of oxazolone with other amino acids forms tripeptides. Furthermore, the chirality of the reacting amino acids is preserved in the oxazolone product, and strong chiral selectivity is observed when converting the oxazolone to tripeptide. This last fact ensures that optically impure amino acids will undergo chain extension to generate pure homochiral peptides. Peptide formation in bulk by wet-dry cycling shares a common pathway with the microdroplet reaction, both involving the oxazolone intermediate.
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Registered trials
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